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cupertino neighborhood guide · property nerds® at compass
Homestead Villa, Cupertino Homes for sale, recent sales and a Property Nerd’s guide
A 1952 tract and later cluster homes and condos in Cupertino's north tip, boxed in by I-280, Hwy 85 and Homestead Road, with Stevens Creek winding through. It stayed county land until 1980.
Homestead Villa by the numbers
homestead villa by the numbers · live from the mls
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Calculated in your browser from MLS data for Homestead Villa: Homestead Rd, Hwy 85, I-280 and the Los Altos line (city planning-area outline). Sales are single-family homes, townhomes and condos.
homes in homestead villa · live from the mls
Homes for sale, for rent and recently sold in Homestead Villa
Every active listing, rental and closed sale in Homestead Villa from the MLS, updated automatically, with a map of the neighborhood outline.
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Listings come from MLSListings and other MLSs through IDX and show their listing brokerage; confirm details with the listing agent. The map outline is the neighborhood boundary used by our listing search (Homestead Villa: Homestead Rd, Hwy 85, I-280 and the Los Altos line (city planning-area outline)); it may not match every local definition.
the story
How Homestead Villa came to be
Homestead Villa is the corner of Cupertino that freeways drew. I-280 runs along its south side, Hwy 85 along its east side, and Homestead Road, the city line with Sunnyvale and Los Altos, along the north. Stevens Creek cuts through the middle on its way north toward Los Altos and Mountain View. The whole pocket covers about 55 acres in the city's planning map, holding tract houses, cluster homes and condominiums.
The original tract came first. County assessor records date the houses on Barranca Drive, Caroline Drive, Hibiscus Drive, Peninsular Avenue and Wallace Drive to about 1952, when this was unincorporated Santa Clara County land. Cupertino incorporated in 1955 and annexed the land around the tract within a few years: the city's annexation records show the Homestead Road frontage and the Maxine Avenue side coming in during 1956, and Acacia Way in 1960. Most of the 1952 tract stayed county land, an island inside the city, until a 28.8-acre island annexation named Homestead Villa took effect in November 1980.
Infill filled the edges. The cluster homes on Sweet Oak, Bitter Oak and Lucky Oak streets went up in 1973, with a second Lucky Oak group in 1980; six duplex lots on Maxine Avenue date to 1974; the Woodspring condominiums on Homestead Road followed in 1984; and six houses on Acacia Way were built in 2007.
streets and homes
The streets and the houses
There are only a few ways in, all from Homestead Road. Barranca Drive enters across from Belleville Way and angles southwest to Peninsular Avenue; Wallace Drive and Hibiscus Drive connect it east to Maxine Avenue, which runs from Homestead Road south to Caroline Drive beside I-280. Acacia Way, Lucky Oak Street, Sweet Oak Street and Homestead Court (the Woodspring entrance) are short streets off Homestead Road. With freeways on two sides and the creek in the middle, no street here continues through to another neighborhood.
The 1952 houses sit on R1-10 lots with a median of about 9,500 sq ft. Assessor records show about 14 of the roughly 90 tract lots carrying a build year of 1990 or later, so most original houses are still standing. The six Maxine Avenue duplex lots are zoned R2-4.25i, and in Cupertino an 'i' designation limits buildings to one story and 18 feet. The Oak-street clusters are zoned R1C, the city's single-family cluster zone, on lots of about 1,400 to 2,000 sq ft, and Woodspring is a planned-development condominium site.
Stevens Creek winds between the 1952 streets and the Oak-street clusters, and it shapes the hazard maps more than anything else here. The city's parcel data flags about 27 parcels, mostly on Barranca Drive, Lucky Oak Street and Peninsular Avenue, as touching FEMA's floodway or AE zone, and about 126 of roughly 266 parcels, including the Oak-street clusters, as inside the city's mapped liquefaction or slope-instability zones.
streets in homestead villa
- Homestead Road
- Barranca Drive
- Caroline Drive
- Hibiscus Drive
- Hibiscus Court
- Maxine Avenue
- Peninsular Avenue
- Wallace Drive
- Acacia Way
- Sweet Oak Street
- Bitter Oak Street
- Lucky Oak Street
- Homestead Court
parks and places
Parks, shops and landmarks near Homestead Villa
- shopping
Homestead Road and Foothill Expressway
The shopping center at the west end of the neighborhood, on the Los Altos side, has a Trader Joe's at 2310 Homestead Rd. according to OpenStreetMap, about 0.3 mile from the middle of Homestead Villa.
- park
Rancho San Antonio
Reached from Foothill Boulevard via Cristo Rey Drive, about 1.5 miles away. Midpen manages the 2,180-acre preserve and the adjoining 293-acre county park, with more than 25 miles of trail and Deer Hollow Farm.
- park
Varian Park
The nearest Cupertino city park, about 0.7 mile south on the other side of I-280 (by road via Foothill Boulevard). The city lists 6.3 acres with a playground, baseball, tennis, picnic tables and barbecue pits.
- landmark
Stevens Creek
The creek runs north through the neighborhood under I-280 and Homestead Road toward Los Altos and Mountain View. FEMA's flood maps include a regulatory floodway along this stretch.
- landmark
Homestead High School
The Fremont Union High School District campus at 21370 Homestead Rd., about 0.8 mile east on the far side of Hwy 85, between Homestead Road and I-280.
schools and commute
School districts and getting around
School districts
Homestead Villa is served by the Cupertino Union School District for kindergarten through eighth grade and the Fremont Union High School District for high school. The closest public campuses are just across Homestead Road in Sunnyvale: CUSD's West Valley Elementary (1635 Belleville Way) and Cupertino Middle School (1650 S. Bernardo Ave.), each about 0.4 mile from the middle of the neighborhood. FUHSD's Homestead High School is about 0.8 mile east. Attendance boundaries change, so check the exact address with CUSD's school locator and FUHSD's boundary maps rather than assuming the nearest school.
Cupertino Union guide · Fremont Union guide · Silicon Valley school districts
Getting around
- Hwy 85 has ramps to Homestead Road at the neighborhood's northeast corner, and the Hwy 85/I-280 interchange sits at its southeast corner.
- I-280 runs along the south edge; Foothill Boulevard crosses it about 0.4 mile west of the middle of the neighborhood (straight-line) and continues north as Foothill Expressway.
- VTA Route 51 stops at Foothill and Homestead on its run between Mountain View and West Valley College; Route 55 serves De Anza Boulevard at Homestead Road, about 1.5 miles east.
- Caltrain: Sunnyvale station is about 3.4 miles northeast and the Mountain View Transit Center about 4.1 miles north (straight-line).
- Homestead Road is a direct east-west route to Sunnyvale, Santa Clara and the Cupertino Village shops at Wolfe Road, about 2.6 miles east.
nerd notes
Buying or selling in Homestead Villa: what we check
Buying here
- Know which of the four housing types you're looking at: R1-10 tract house, R2-4.25i duplex (one story and 18 feet maximum), R1C cluster home, or Woodspring condominium. Each has different rules for additions, ADUs and SB 9.
- For cluster homes and condominiums, read the HOA documents, budget and reserve study before you remove contingencies; ask what the association covers for roofs, exteriors and common areas.
- Most of the 1952 tract was county land until 1980. For older additions and conversions, check permit records with both Santa Clara County and the City of Cupertino.
- Check hazard zones parcel by parcel: about 27 parcels touch FEMA's floodway or AE zone along Stevens Creek, and nearly half the parcels sit in the city's mapped liquefaction or slope-instability zones. Read the natural hazard disclosure and check FEMA's map for the exact address.
- Freeways border two sides, so visit at different times of day, and on a 1950s house have the inspector look at electrical, foundation, sewer lateral and any unpermitted work; expect the federal lead-paint disclosure on anything built before 1978.
Selling here
- Say which housing type and zoning the home has; buyers here compare tract houses, cluster homes and condos side by side.
- Gather permits from the county (before November 1980) and the city (after) for the 1952 tract houses.
- For cluster homes and condos, have the HOA resale package ready early so buyers can review it inside their contingency period.
- Give real distances: Hwy 85 and I-280 access, the Homestead Road shops, and the CUSD and FUHSD campuses nearby, with a note that buyers should confirm school assignment with the districts.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Homestead Villa questions, answered
Is Homestead Villa in Cupertino?
Yes. Most of the 1952 tract was unincorporated county land surrounded by the city until a 28.8-acre island annexation took effect in November 1980; the land now under the cluster homes and the Homestead Road frontage had joined in 1956. Across Homestead Road the addresses are in Sunnyvale or Los Altos.
What kinds of homes are there?
Four kinds: about 90 houses in the 1952 tract on lots near 9,500 sq ft, about 80 small-lot cluster homes on Sweet Oak, Bitter Oak and Lucky Oak streets from 1973 and 1980, six one-story duplex lots on Maxine Avenue, and the 67-unit Woodspring condominium complex from 1984, plus six houses on Acacia Way from 2007.
Which schools serve Homestead Villa?
The Cupertino Union School District and the Fremont Union High School District. West Valley Elementary and Cupertino Middle School are just across Homestead Road and Homestead High is about 0.8 mile east, but boundaries change, so confirm the address with each district.
Is the area in a flood zone?
Parts of it. FEMA maps a floodway and AE zone along Stevens Creek, which runs through the middle, and the city's parcel data flags about 27 parcels as touching them. Most of the rest are in FEMA's 0.2-percent-annual-chance area, outside the Special Flood Hazard Area. Check the FEMA map and the natural hazard disclosure for the specific address.
How close is the freeway?
Very. I-280 forms the south edge and Hwy 85 the east edge, with Hwy 85 ramps at Homestead Road. That is handy for commuting; visit at rush hour to judge sound for yourself.
talk to a property nerd
Thinking about Homestead Villa? Let's run your numbers.
Eric, Janelle and the Boyenga Team have sold more than 2,520 Silicon Valley homes, $2.6+ billion in all, since 1996. Get a value, a plan, or a straight answer about a street.
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